Cyclopiazonic acid, CPA
Catalog #:
IN0067| IN0068-5mg | USD52.0 |
Synonyms: Cyclopiazonic acid, CPA, 10-acetyl-9-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-11h-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-11-one, 9H-Pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6a.alpha.,11a.beta.,11b.alpha.)- alpha-Cyclopiazonic acid
IUPAC Name:
(6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Functional Activity:
Cyclopiazonic acid (CPA)inhibits the sarcoplasmic reticulum Ca2+-pump.
It is a toxic fungal secondary metabolite. Chemically, it is an indole tetramic acid.
CPA was originally isolated from Penicillium cyclopium and subsequently from other P. cyclopium, Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor.
Caution: This product is a Dangerous Good (UN3462) and carries a $10 dangerous goods packaging fee.
Technical Data:
M.Wt: 336.39
Formula: C20H20 N2O3
Solubility: Soluble in 5 mM in ethanol and in 100 mM in DMSO
Purity: >98%
Storage: Dessicate at -20°C
CAS No.: 18172-33-3
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References for Cyclopiazonic acid (CPA) :
1. Liu, X. and Walsh, C. T. Characterization of cyclo-acetoacetyl-L-tryptophan dimethylallyltransferase in cyclopiazonic acid biosynthesis: substrate promiscuity and site directed mutagenesis studies. Biochemistry, 48: 11032-11044, 2009.
2. Liu, X. and Walsh, C. T. Cyclopiazonic acid biosynthesis in Aspergillus sp.: characterization of a reductase-like R* domain in cyclopiazonate synthetase that forms and releases cyclo-acetoacetyl-L-tryptophan. Biochemistry, 48: 8746-8757, 2009.
3. Seshime, Y., Juvvadi, P. R., Tokuoka, M., Koyama, Y., Kitamoto, K., Ebizuka, Y., and Fujii, I. Functional expression of the Aspergillus flavus PKS-NRPS hybrid CpaA involved in the biosynthesis of cyclopiazonic acid. Bioorg Med Chem Lett, 19: 3288-3292, 2009.
4. Moldes-Anaya, A. S., Asp, T. N., Eriksen, G. S., Skaar, I., and Rundberget, T. Determination of cyclopiazonic acid in food and feeds by liquid chromatography-tandem mass spectrometry. J Chromatogr A, 1216: 3812-3818, 2009.
5. Zhang, W. B. and Kwan, C. Y. Unrepeatable extracellular Ca2+-dependent contractile effects of cyclopiazonic acid in rat vascular smooth muscle. Eur J Pharmacol, 610: 81-86, 2009.
6. Laursen, M., Bublitz, M., Moncoq, K., Olesen, C., Moller, J. V., Young, H. S., Nissen, P., and Morth, J. P. Cyclopiazonic acid is complexed to a divalent metal ion when bound to the sarcoplasmic reticulum Ca2+-ATPase. J Biol Chem, 284: 13513-13518, 2009.
